👩🏻‍🏫 Krysten Conner

🚫pipeline anxiety l Terrible dancer l Always a Teacher 🦄🦄🦄 ex Outreach, Salesforce, Tableau 👉🏼👉🏿👉🏽 Click bell/top right to be notified when I post 🔔

You’re not trying to “hit quota.”

You’re trying to become the kind of seller who can repeat top performance across territory changes, market shifts, and new quarters.  

Not with luck. Not with late-quarter heroics. With a *system*.


Most AEs can have a great quarter.  

Consistent top performers have a way of operating that creates sustainable, repeatable results.

That’s what I teach.


I spent 12 years selling Enterprise deals at Salesforce, Tableau, and Outreach. I eventually broke records, 14X’d territory expectations, and ran a 47.6% win rate. But I didn't start that way.

The biggest shift I made wasn’t a new script or a new tech stack.

It was learning how to sell like a top performer actually sells:

✅Reduce confusion (connect the dots, make WIIFM obvious, reduce friction)
✅Run discovery that’s **direct and tactful**
✅Multi-thread early and build real champions 
✅Win the 95% of the sales cycle that happens between meetings
✅Act like a **Sherpa**: guide the buying journey so your buyer never has to guess what’s next


If you’re a rep who’s already performing and you’re thinking:

“I don’t want to be a one-hit wonder.”  

“I want to be on the leaderboard… consistently.”  

“I want make my process sustainable, so my results are sustainable.”

I'm your person.


Here’s what clients say after working together:
 👉 “I closed a $2.66M ARR enterprise deal after 26 months of work, and Krysten's coaching was critical in helping get it across the line."
 👉 "I set an ambitious goal when I started: hit at least 200% of quota in my first full quarter. Working with Krysten helped me turn that goal into reality. I hit 225% and closed the largest deal ever won by a new rep."
👉 "Wanted to thank you and let you know I closed my biggest deal ever in December, $2.2mil TCV, 3 year agreement. We were stuck at one stage with a start date that would have caused the deal to slip from Q4 to Q1, I used your COI principles and in-particular a visual graph that showed what the actual cost was of starting now -vs- later. Ended up getting it done 🤩 Thank you!!"


You don’t need another sales theory.
You need someone who’s been in your shoes - and knows how to win big deals now.

Let’s work together: krystenconner.com


🟢 I offer 1:1 coaching for individual reps, and workshops for sales teams who want to win bigger, faster, and more often.


Browse client wins here: https://www.linkedin.com/in/krystenconner/details/recommendations/



💫"We pay for every lesson with either time or money. And we use the currency we value least."
         -Alex Hormozi

Member

I walked away from the biggest deal of my career. $13.7M. Would've blown my quota out of the water.

But here's what that "loss" taught me...

The CEO had everything: 
✓ A problem we could solve 
✓ Agreement he HAD the problem
✓ Desperate need to fix it 
✓ Budget approved

But one thing kept nagging at me.

Every meeting, he'd ask about customization. 
About "partnering" to build features.
About source code access. 

Classic Build vs. Buy syndrome.

After our 5th in-person meeting (yes, FIVE), I finally saw it clearly.

This wasn't a buyer. This was a builder trapped in a buyer's process.

His personality screamed "I'll do it myself." 
His energy peaked when discussing his team's capabilities.
His questions focused on HOW we built it, not WHAT it could do. 

So I made the call that physically hurt:

I removed it from my pipeline.

My manager: "Are you SURE?" 
My financial plan: "But the commission..." 
My ego: "You're giving up."

Here's what happened next:

→ Freed up 30+ hours that month 
→ Focused on a $1.8M deal that actually wanted to buy 
→ Closed 3 other deals while he was still "evaluating" 
→ Finished with my best year ever

And that CEO? 
18 months later, still building. 
Still solving the same problem.

The real lesson?

Not every deal is YOUR deal.

Some buyers aren't buyers—they're builders in disguise. And the time you waste convincing them is time you could spend closing real deals.

Three questions I now ask myself:

1./ Are they asking about outcomes or architecture?
2./ Do they light up more about building or buying?
3./ Is their real goal independence or results?

If the answers point to "building," I'm out. No matter the size.

Because the best deals aren't always the biggest ones. 
They're the ones that actually close.

What deal have you walked away from that taught you the most?

Krysten Conner

I help AEs win 6-7 figure deals to overachieve quota & maximize their income l ex Salesforce, Outreach, Tableau l Training B2B Sales teams & Individual sellers l 3x Top 100 Most Powerful Women in Sales by Demandbase

Here are the 8 questions CFOs ask before every software purchase. (And they're brutal.)

Every champion I've ever worked with eventually hits a moment of panic:
"What do I say when Finance starts asking the hard questions?"

👉 Most CFOs won't tell you what they're really thinking. They just kill your deal silently.

But I've spent 13 years watching Enterprise deals die in Finance. And I've learned what CFOs actually need to hear.

Here are the 8 questions every CFO is asking behind closed doors, courtesy of the "Only CFOs" newsletter, as highlighted by  Nate Nasralla :

1. Why do we need [X product] now? We were fine before. 
2. What bucket does this fall into, and can you quantify it?
-----Improves efficiencies
-----Increases revenue
-----Mission critical (e.g. cybersecurity)
-----"Candy": nice-to-have tool that doesn't really fit into the above groups 
3. Is the spend in the budget? If not, how will you make up the difference? 
4. How does this tool tie into our company objectives for this year? 
5. What tools do we already have that do something similar? And if similar tools exist, why can't we use those? 
6. Implementation: What are the people / time requirements? 
7. Support costs: Will we need to upgrade soon to enterprise /other tier? 
8. Pricing:
-----If usage-based pricing: I want a detailed analysis on how pricing works and modeling for what our planned usage will look like.
-----If seat-based pricing: I don't want to buy a bunch of extra seats for planned growth. That got a lot of people in trouble when headcount growth halted and layoffs happened.

The deal-killers? Numbers 1, 3, and 5.

At Salesforce, I watched 6-7 figure deals die instantly when the champion couldn't answer those 3 questions clearly.

What are the best way's you've found to prepare your champions for these conversations?

Which of these questions makes your Champions the most nervous? 

PS - Find this helpful? You might like my newsletter. Over 7,000 sellers getting valuable nuggets every week. More details in my bio. Hope to see your name on the list!

Jordan Benjamin 🧘

Principal 1 Agency Partner Sales Consultant

I Help Sellers Crush Quota Without Burnout | ex-HubSpot | 🎙 Peak Performance Selling Podcast

𝗪𝗮𝗻𝘁 𝘁𝗼 𝗰𝗼𝗻𝘁𝗶𝗻𝘂𝗲 𝗰𝗿𝘂𝘀𝗵𝗶𝗻𝗴 𝘆𝗼𝘂𝗿 𝗾𝘂𝗼𝘁𝗮 𝘄𝗵𝗶𝗹𝗲 𝗰𝗿𝗲𝗮𝘁𝗶𝗻𝗴 𝘁𝗵𝗲 𝗹𝗶𝗳𝗲 𝗼𝗳 𝘆𝗼𝘂𝗿 𝗱𝗿𝗲𝗮𝗺𝘀?
𝗠𝗮𝗻𝘆 𝗽𝗲𝗼𝗽𝗹𝗲 𝘁𝗵𝗶𝗻𝗸 𝗶𝘁'𝘀 𝗼𝗻𝗲 𝗢𝗥 𝘁𝗵𝗲 𝗼𝘁𝗵𝗲𝗿. 𝗜𝘁 𝘀𝗵𝗼𝘂𝗹𝗱 𝗯𝗲 𝘆𝗲𝘀, 𝗔𝗡𝗗!

🟢 Fact #1. Sales should be one of the most rewarding professions on the planet, but
🔴 Fact #2. According to most recent research 𝟕𝟎% 𝐨𝐟 𝐬𝐞𝐥𝐥𝐞𝐫𝐬 𝐫𝐞𝐩𝐨𝐫𝐭 𝐭𝐡𝐞𝐢𝐫 𝐦𝐞𝐧𝐭𝐚𝐥 𝐡𝐞𝐚𝐥𝐭𝐡 𝐚𝐬 𝐩𝐨𝐨𝐫 𝐨𝐫 𝐟𝐚𝐢𝐫

*𝗪𝗵𝘆 𝟳𝟬% 𝗼𝗳 𝘀𝗲𝗹𝗹𝗲𝗿𝘀 𝗮𝗿𝗲 𝘀𝘁𝗿𝘂𝗴𝗴𝗹𝗶𝗻𝗴* 📉
Most sellers are hungry, driven and motivated to make serious 💰 🤑
But, they live in the land of “what have you done for me lately?” 
They know there’s always more to be done AND
They’ll be back to zero again soon
Even top performers get let go

Sustaining success in sales takes 2 key skills: 𝑯𝒖𝒏𝒈𝒆𝒓 and 𝙋𝙨𝙮𝙘𝙝𝙤𝙡𝙤𝙜𝙮 🧠
Most sellers have #1.  
But they haven’t been taught #2, to train their subconscious to work FOR them. 📈
Most sellers I talk to, think their manager will teach them everything they need for success
That’s a lie your managers job is to solve for the company & then themselves
Another band-aid is NOT the answer 
But they don't have a system

James Clear says it best:
“𝗬𝗼𝘂 𝗱𝗼 𝗻𝗼𝘁 𝗿𝗶𝘀𝗲 𝘁𝗼 𝘁𝗵𝗲 𝗹𝗲𝘃𝗲𝗹 𝗼𝗳 𝘆𝗼𝘂𝗿 𝗴𝗼𝗮𝗹𝘀. 𝗬𝗼𝘂 𝗳𝗮𝗹𝗹 𝘁𝗼 𝘁𝗵𝗲 𝗹𝗲𝘃𝗲𝗹 𝗼𝗳 𝘆𝗼𝘂𝗿 𝘀𝘆𝘀𝘁𝗲𝗺𝘀.”


⭐𝐓𝐡𝐞 𝐏𝐞𝐚𝐤 𝐏𝐞𝐫𝐟𝐨𝐫𝐦𝐚𝐧𝐜𝐞 𝐒𝐞𝐥𝐥𝐢𝐧𝐠 𝐒𝐲𝐬𝐭𝐞𝐦⭐
Helps you:
✅ Use modern science + 2,000 year old wisdom to crush your biggest goals 💰🏡 🛫 👨‍👨‍👧‍👦 
✅ Understand the psychology of what makes people take action
✅ Get the most leverage from each hour in the day
✅ Create a system to elevate your career now
✅ Get free from the sales hamster wheel
✅ Feel better & make more $$

*𝗛𝗢𝗪 𝗪𝗘 𝗚𝗘𝗧 𝗥𝗘𝗦𝗨𝗟𝗧𝗦*
Small personalized changes that deliver massive results
This system has been delivered to 1000s of professionals and has been refined over 5 years to get you the most impact in your life. 
In a short time frame, with simple changes you can create the life of your dreams.

*𝐖𝐇𝐎 𝐈𝐒 𝐈𝐓 𝐅𝐎𝐑?*
High achievers. Sellers that are not going to be complacent with a good life. 
Professionals who know they have more to give to the world and make great $$$ too.

𝗪𝗛𝗘𝗡 𝗬𝗢𝗨’𝗥𝗘 𝗥𝗘𝗔𝗗𝗬 𝗛𝗘𝗥𝗘 𝗔𝗥𝗘 ✌️ 𝗪𝗔𝗬𝗦 𝗪𝗘 𝗖𝗔𝗡 𝗛𝗘𝗟𝗣
1️⃣ DM Me directly. I’m happy to connect and hear what you're working towards and if we can help.
2️⃣ Book a free clarity call to learn if it fits for you (15 min)
MyCoreOS.com/meetings/jbenj/clarity-call

Principal Partner Sales Manager

$1.1Mil dollar club
Top 15 Global Sales Rep
Coached Agency Owners & Sales Teams to Drive Triple Digit revenue growth

I spent ~$10,000 last year learning LinkedIn
From some of the best in the world
Here are my list of things NOT to do:

1. Don't post all about yourself
-Nobody will share that
Add value AND be a real human

2. Don't get stuck in a pod
-It has short-term rewards, but doesn't win the long game
Find people you can genuinely connect with

3. Don't be a d*ck
-The algo loves controversial, spicy takes...but taking others down
Isn't the game I want to be playing

4. Don't rely on AI
-Sure it's easy to write everything and all comments with AI
It takes the human out of it and is a race to the bottom

5. Don't believe you deserve anything
-You'll see people with a smaller following, less experience, etc.
Have posts get MASSIVE virality... and that's OK

6. Don't chase the algorithm
-It's so far out of your control
Write for yourself one, two, or ten years ago

7. Don't quit
-Consistency in showing up is the key to winning
Keep showing up and your life can change

What else should you avoid?!

Helping Sellers Crush Quota And Not Burnout | 6X P-club @ HUBS | Helped 172+ Sellers & Leaders Crush Goals & Life Last Year

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👩🏻‍🏫 Krysten Conner

Jordan Benjamin 🧘

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taplio

The Battle

👩🏻‍🏫 Krysten Conner

Jordan Benjamin 🧘

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}👩🏻‍🏫 Krysten Conner's LinkedIn Performance

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